Brad Mills is a Bitcoin OG (in since 2011), entrepreneur, and angel investor. In this episode, we talk about what it actually looks like to think long-term in Bitcoin, how he invests without selling, and why “AI agents + Bitcoin” might be the first truly mainstream crypto use case.
We get into real founder stuff too: leadership failures, scaling mistakes, decision fatigue, and how Brad rebuilt his habits using a “proof of work” mindset.
What we cover:
Brad’s first “business” at 8 years old, and the Facebook app that hit massive scale
The moment he realized “buy and hold Bitcoin” outperformed his highest-effort businesses
Borrowing against Bitcoin: why LTV discipline matters and how people get wiped out
Why gold confiscation (6102) is not the same risk model as Bitcoin custody today
Quantum risk: what’s real, what’s noise, and how upgrades likely happen
Why AI agents choosing Bitcoin is a bigger deal than retail adoption
“Citadel mind and body”: applying Bitcoin-style consistency to health and relationships
Books that actually changed his execution
Chapters / Timestamps
00:00 Intro, “Bitcoin is up 3x since 2022” 01:40 Brad’s first business at 8 years old 04:00 Growing up in poverty, learning to hustle 04:30 Hacky sack business and early entrepreneurship 05:40 “How do I make money online?” and getting scammed 06:15 The Facebook “Roll Up The Rim” app and the cease & desist 07:10 Monetization at scale, then getting crowded out 08:40 Hiring 17 people, leadership reality check 11:55 When Bitcoin outperformed the entire company 12:10 Brad’s first Bitcoin in 2011 and the early volatility lessons 15:00 Failed mining partnership and why he stopped “doing too much” 19:00 Trading strategy vs just holding Bitcoin 21:05 Becoming an angel investor (Bitcoin-only) 21:45 Borrowing against Bitcoin, loans, and LTV discipline 28:15 Interest rates and banks eventually offering BTC loans 30:00 Canada, optionality, and the sovereign individual thesis 33:00 Gold confiscation (6102) and why it’s often misunderstood 36:05 Self-custody vs “in the bank vault” risk 38:45 Capital controls and how Bitcoin changes the game 41:30 Epstein/Bitcoin origin claims and why decentralization makes it irrelevant 45:20 This downturn: what feels different this cycle 50:55 Is quantum Bitcoin’s biggest risk? 52:00 Quantum soft fork talk + Saylor’s quantum task force 56:10 “Quantum treasure hunt” and lost coins as a volatility catalyst 01:00:25 Portfolio updates, Maple private AI compute, AnchorWatch insurance 01:02:15 Square/Cash App Bitcoin payments and orange-pilling merchants 01:03:45 AI agents using Bitcoin as default money 01:10:15 OpenClaw as “translator” for non-technical builders 01:12:30 CLAWI.AI, Mac mini vs VPS setups 01:12:40 Token burn reality ($150–$200/day) 01:13:45 “Citadel mind and body” and proof-of-work habits 01:23:00 Book recs: Buy Back Your Time, The Big Leap, If the Buddha Married 01:24:35 Wrap
The Arena The Arena is a private Skool community for SaaS founders who are actively building and selling. I share real-time decisions, experiments, and assets as I use them while growing a bootstrapped SaaS.
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